155 properties for sale in Old Bayside

Wrap yourself in private, secluded elegance in this mid-century modern lakefront retreat. It's located in the sought after community of Lake Karylbrook, near the Chesapeake Bay and town of Chesapeake Beach. The lot encompasses 3.44 acres of private woods with approximately 270 ft of lake frontage. Exterior re-claimed redwood blends the home naturally with the surrounding forest. Enter your home through the huge solarium with the colors and fragrances of your favorite plants to welcome you. The solarium gives you a year round growing season. Lemons, figs, and peppers do well in it. The interior great room features warm re-claimed redwood walls, continuing the theme of connection to the surrounding outdoors. The main level features a large, open floor plan with outdoor views and deck access from all rooms. Walk directly out from the open great room to deep-breathe fresh air scented by evergreens. From either main level bedroom step out in complete privacy. No one can see you. Before or a

Welcome to 8560 Saint Andrews Drive, an opportunity to own a home with incredible potential in the desirable Highlands neighborhood. This 3-bedroom, 1 full and 1 half bath home offers the chance to move in, make it your own, and build sweat equity along the way. The home is priced with its potential in mind and features a detached two-car garage, plenty of possibilities, and a great setting for buyers looking to create a home that truly fits their style. With some updating and personal touches, this property could be transformed into something special without having to take on a complete renovation from day one. Whether youre a first-time buyer, someone who enjoys home projects, or simply looking for an opportunity to add value over time, this home offers a great foundation to work with. Located just outside of downtown Chesapeake Beach, youll enjoy convenient access to the Chesapeake Bay waterfront, boardwalk, Rod N Reel, local restaurants, shopping, and everything this popular beach

This exceptional home is move-in ready and offers the space, updates, privacy, and location you've been looking for. Don't miss your opportunity to make it yours! Welcome home to this beautifully maintained 4-bedroom, 2-bath split-foyer nestled on a private, expansive. 97-acre lot! Offering generous living space, thoughtful updates, and an oversized 780 sq. Ft. two-car garage. *great for the mechanic*. This move-in-ready home combines comfort, convenience, and privacy in an ideal location. The upper level features a bright and inviting living room, dining room, and an updated kitchen complete with granite countertops and stainless-steel appliances. Three spacious bedrooms and a full bath complete the main level. The finished lower level provides even more living space with a large family room featuring a cozy wood stove, a fourth bedroom, laundry room, and a beautifully updated full bath with a custom ceramic-tile shower. Direct access to the oversized two-car garage adds exceptional e

Come experience the best of one-level living in this sprawling, impeccably maintained rambler, set on a beautiful 2-acre private lot in sought after community of Tall Oaks. From the moment you step into the spacious foyer and see the gleaming hardwood floors throughout, youll feel right at home. Plantation shutters throughout add an elegant finishing touch. The bright and sunny living room flows seamlessly into the dining area and upgraded kitchen, featuring beautiful granite countertops. Just a step down, the spacious family room offers a slider leading to the rear Trex deck, complete with a retractable awningperfect for relaxing or entertaining while overlooking the private backyard and your own 4-foot-deep inground pool. A detached outbuilding with a concrete floor provides the perfect space for storing tools, equipment, and all your toys. Back inside, the spacious primary suite features his-and-her closets and a recently renovated primary bathroom with a gorgeous walk-in tile showe

Welcome Home! Welcome to this beautifully updated 4-bedroom, 3.5-bath home, perfectly situated just off Route 2 for an easy commute to Joint Base Andrews, Annapolis, and Washington, D. C.offering the ideal blend of convenience, comfort, and everyday living. Thoughtfully updated throughout, this home features modern finishes, spacious living areas, and exceptional functionality. The main level showcases beautiful upgraded engineered wood flooring and a stunning updated kitchen featuring granite countertops and Bosch appliances. Just off the kitchen, the gorgeous mudroom with custom built-ins provides the perfect combination of organization and storage. The updated bathrooms add to the home's fresh, polished feel, while the finished basement offers even more living space with brand-new flooring, custom built-ins, and a full bathroom. Whether used as a family room, home office, guest suite, playroom, or additional entertainment space, the possibilities are endless. Step outside onto the b

Your Chesapeake Beach Home Awaits! Imagine summer afternoons spent splashing in your own above-ground pool, relaxing on the spacious deck under the retractable awning, and enjoying evenings outside with the people who matter most. Welcome to 4006 Chesapeake Ave in Chesapeake Beach, where everyday living comes with room to unwind and make memories. This 4-bedroom, 3-bath home offers 1,785 square feet of comfortable living space, with a welcoming front porch, attractive landscaping, and inviting outdoor areas. Whether you're hosting a backyard barbecue, enjoying a quiet morning coffee, or watching the kids play outside, there's space to enjoy life at your own pace. Inside, four bedrooms offer flexibility for family, guests, a home office, or hobbies. Outside, the deck and pool create a natural gathering place for warm-weather fun, while the covered outdoor space lets you enjoy the fresh air in comfort. And the location adds even more to love. Enjoy the Chesapeake Beach lifestyle, with ne

Assumable va loan at 3.375%! Qualified buyers can take over the sellers low rate, subject to lender approval. Rare opportunity to own directly on the Chesapeake Bay in Windward Key, where bayfront homes seldom come on the market. This 4-level, 3-bedroom, 3-full-and-2-half-bath coastal townhouse in Chesapeake Beach sits directly on the water with expansive Bay views and a private community sandy beach. Balconies on every level offer front-row sunrise views over the water and shifting sky and watercolor at dusk. The kitchen window frames its own daily sunset. The kitchen features Blue Pearl granite countertops, Dura Supreme semi-custom cabinetry in the white painted Arcadia Classic Deluxe finish, a 2022 LG stainless French-door smart refrigerator with ice and water dispenser, and a GE Profile stainless convection range. A gas fireplace warms the main living area, and motorized Hunter Douglas remote-controlled blinds cover the kitchen and both sliding glass doors, opening the Bay view or

Nestled in the charming Bayview Hills community, this delightful split-level home offers a perfect blend of comfort and style. With 2,368 square feet of thoughtfully designed living space, this home features four spacious bedrooms and three full bathrooms, ensuring ample room for relaxation and privacy. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and breakfast areas. The kitchen features stainless steel appliances, a large breakfast bar and plenty of cabinet space for everyday living and entertaining. The fully finished basement provides additional living space featuring a spacious recreation room with a cozy fireplace and brick hearth, a bedroom, full bathroom, additional storage, and convenient garage access. Outside, enjoy the deck and custom stamped concrete patio, providing the perfect setting for outdoor entertaining or simply relaxing at the end of the day. Beautiful landscaping adds to the homes curb appeal, while the attache

Welcome to the one you've been waiting for. Nestled in 3.3 acres is this beautiful single family home with all the bells and whistles you can wish for. Greeted by a large front porch that overlooks the long driveway with extended parking. Fall in love with the brand new gleaming hardwood floors throughout your main level and upper level. With five bedrooms, four full baths, one half bath. Bedrooms have room for everyone even with two masters upstairs Includes two large garages and a finished walkout lower level. Open floor plan gives plenty of space for entertaining with a gourmet kitchen and brand new shiny counter tops with full height backsplash with a waterfall. Sunroom/ Dining flow right across your large wrap around composite deck. Enjoy gorgeous view of the property that overlook the large above ground pool. Stairs connect down to another deck and concrete patio for multi level entertainment. The fully finished walkout basement adds more living space with plush carpet and anothe

Just 2 houses from the Chesapeake Bay and you do have some views from the house. There is a deck between the house and the large shed that has quite nice views of the Bay. This is a great home or home away from home on the weekends! Right now is a weekend get away but it also has the ability to be used for some commercial uses if you would desire. It has a great big garage that the house sits on that holds at least 3 cars, back to back as well as a driveway. Don't like stairs? There is a lift through the garage taking you to the main level! Lovely marble flooring on the main level with large recreation room, kitchen, small bedroom and 2 full baths. Upstairs you will have a spacious primary suite as well as another good size bedroom which have relatively new carpeting. This property has so many different possibilities, guest cottage, full time home, week end escape, commercial possibilities, work at home and use for business, etc. Come take a look and make it yours. Sold in AS IS condit

New roof! Bigger than you think and full of surprises! This brick rambler offers 3 bedrooms, 3 full baths, a finished walk-out basement, inground pool, detached two-car garage, and an additional structure with potential for an office, studio, or in-law suite, all on a private, wooded acre with no HOA. Set on a full acre with wooded side and rear areas that provide plenty of privacy, this Owings home offers convenient main-level living with room to spread out. Hardwood floors, floor-to-ceiling windows, and a double-sized living room with bay windows create an inviting main level, centered around a large masonry fireplace with pellet stove. The updated kitchen features cherry wood cabinetry, Corian countertops, and a tiled backsplash, opening to an informal dining area. A separate formal dining room offers flexibility for an office, playroom, or additional living space, while sliding glass doors lead to the backyard, pool area, and decks. The finished walk-out basement adds even more usa

You'll love the private outdoor spaces from this beautifully maintained townhome-including a large composite deck that backs to woods, and an outdoor patio from the walk out basement! Located in the desirable San Francisco by the Bay community, you'll enjoy just a short walk to the Chesapeake Bay, beaches, restaurants, shopping, and the charm of North Beach and Chesapeake Beach! The main level welcomes you with a beautiful eat-in kitchen featuring abundant cabinet and counter space, a convenient pass-through to the living area, soft-close cabinet hinges, in-cabinet trash and recycling bins, and numerous updated appliancesincluding a new refrigerator (2025), oven and microwave (2024), dishwasher and garbage disposal (2022). A new chandelier enhances the dining area, while the sun-filled living room offers gleaming hardwood floors and sliding glass doors opening to a new 12' x 16' composite deck. Constructed with pressure-treated beams and solar-lighted post caps, the deck was completed

Va assumable loan at (2.75%) Ask for Details! *. Welcome to 8308 Legacy Circlea place to spread out, settle in, and embrace the easygoing Chesapeake Beach lifestyle. Tucked within the Heritage Woods community, this inviting 4-bedroom, 3.5-bath home offers the space, comfort, and flexibility to make everyday life feel a little more special. Picture slow mornings in a sun-filled kitchen, coffee in hand, as the day begins. Luxury vinyl plank flooring creates a stylish, easy-care setting for busy households, while the kitchen is thoughtfully equipped with a refrigerator, range/oven, microwave, dishwasher, disposal, and vent faneverything you need for weeknight dinners, holiday baking, or a casual gathering with friends. With approximately 3,315 finished square feet across the main and upper levels, there is room for everyone to have their own space while still coming together at the end of the day. Four spacious bedrooms upstairs create comfortable retreats, and the conveniently located up

Seller is motivated and welcomes all reasonable offers! Welcome to 1920 Appaloosa Way! This charming 3-bedroom, 2-bath rancher offers the perfect blend of comfortable one-level living and expansive outdoor space on a beautiful 3.2-acre, fenced property. A long driveway leads to the home and provides plenty of parking, along with a very large detached 2-car garage. For those looking for equestrian or hobby space, the property features multiple horse stalls, including a barn with multiple stalls at the front of the property and a 2-stall barn behind the home. The grounds are enclosed with wooden fencing around the property, along with additional metal fencing ideal for dogs. The home also features a heated rear addition, family room with an electric fireplace, and a small shed located behind the garage. With open acreage, multiple outbuildings, fenced grounds, and flexible spaces for horses, pets, hobbies, or storage, this property offers a unique opportunity to enjoy the space and priva

A rare opportunity with room to live, work, store, and create! Zoned TC (Town Center), this property has a multitude of possibilities. Situated on 0.73 acres, this four-bedroom, two-full-bath split foyer offers 2,380 above-grade square feet, a walkout lower level, central air conditioning on the main floor, a deck, and flexible space ready for your vision. The lower level is partially finished to include a finished full bathroom, while providing loads of additional possibilities for future use. Outside is where this property truly stands apart. Enjoy extensive driveway parking, a detached garage/workshop with high clearance doors, and three sheds. This is an ideal setup for a mechanic, vehicle enthusiast, contractor, hobbyist, or anyone seeking substantial workspace and storage. The property also features a private well and a mound septic system. Notable updates include the roof in 2020, septic system in 2020, and HVAC in 2023. Zoned Town Center (TC), the property may offer opportuniti

Welcome to 6430 Dant Drive, where comfortable one-level living meets the space and privacy of a beautiful one-acre setting in sought-after Owings. Offering nearly 2,000 square feet, this inviting 4-bedroom, 2-bath rambler has been thoughtfully cared for and provides the perfect blend of indoor comfort and outdoor living. Inside, a desirable split-bedroom floor plan creates a sense of privacy and separation, while generous living spaces provide plenty of room for everyday life, entertaining and gathering with family and friends. Updated flooring, fresh paint and stainless steel appliances give the home a refreshed, move-in-ready feel. Outside is where this property truly shines. Imagine summer afternoons by the pool, evenings relaxing on the surrounding deck, and weekends enjoying your own expansive backyard. The fenced yard offers plenty of room for pets, play and entertaining, while the one-acre homesite provides the breathing room so many buyers are searching for. A large storage she

Simply stunning and impeccably maintained, this exceptional Huntingtown home offers the perfect combination of elegance, comfort, and thoughtful updates. Ideally situated approximately 36 miles from Washington, DC, 31 miles from Annapolis, and 26 miles from Solomons, this beautiful four-bedroom residence offers two full bathrooms and two half bathrooms, along with an abundance of space for everyday living and entertaining. Adding to its outstanding location, the home is less than 9 miles from the Chesapeake Beach and North Beach waterfront communities and boardwalk. Enjoy easy access to the Chesapeake Bay lifestyle, including waterfront dining, local restaurants, marinas, boating and fishing opportunities, beaches, parks, community events, and the scenic North Beach Boardwalk. Whether enjoying an evening along the waterfront, dining overlooking the Bay, or spending a day on the water, the Chesapeake Beach and North Beach area offers a wonderful coastal destination just minutes from hom

Welcome to 6425 Dant Road in Owings! Situated on a spacious 1.2 acre lot, this beautifully renovated 4-bedroom, 3-bath home offers modern updates and plenty of room to spread out. Recent improvements include new flooring and fresh paint throughout, a beautifully updated kitchen, renovated bathrooms, and new mini-split systems in addition to the existing heat pumps. A versatile bonus room provides the perfect space for a home office, playroom, etc. Outside, enjoy a spacious yard and the convenience of an attached two-car garage. Move-in ready with the major updates already completed, this one is ready to welcome you home!

Welcome to an extraordinary private estate nestled on more than 55 breathtaking acres in the heart of Owings yet only 20 minutes to AAFB and 30 mins to Washington DC, where luxury, elegance, and unmatched seclusion come together to create a truly one-of-a-kind offering. Surrounded by pristine countryside featuring two creeks and a private pond, this remarkable property offers an exceptional lifestyle defined by peace, beauty, and privacy. From the moment you step into the grand open-concept two-story foyer, highlighted by a sweeping staircase and abundant natural light, the home immediately makes a lasting impression. Thoughtfully designed for both upscale entertaining and comfortable everyday living, the main level features a formal dining room ideal for gatherings, while the sophisticated living room currently serves as a beautifully designed music room filled with warmth and character. A well-positioned wet bar between the dining room and kitchen creates the perfect space for hostin

Welcome to Chesapeake Beach. Easy one-level living, a huge detached garage, and the laid-back coastal lifestyle welcomes you! This three-bedroom home offers an easy, functional layout with everything you need on one floor. The spacious living room features large windows that bring in plenty of natural light, while the kitchen offers generous cabinet space and newer stainless steel appliances. Major improvements include a new roof in 2021, new HVAC in 2022 and a newer hot water heater. Outside is where this property really stands out. The massive detached garage is a rare find for the twin beaches and offers you incredible space for vehicles, a workshop, hobbies, storage, or all the beach toys! A large driveway provides plenty of additional parking, and the fenced-in yard gives you room for pets, entertaining, gardening, or relaxing outside. Living in Chesapeake Beach means enjoying everything that makes Northern Calvert County so desirable. Spend weekends along the Chesapeake Bay, walk

Welcome to an extraordinary private estate offering more than 7,000 square feet of refined living space on over 13 breathtaking acres. Pristine landscaping, spectacular views of Herring Bay, rolling pastures, equestrian facilities, and surrounding countryside create an unparalleled lifestyle. Designed by renowned architect George A. Brunatti, AIA, and constructed under the direct supervision of the owners, experienced licensed general and mechanical contractors, this exceptional residence reflects a level of craftsmanship, structural integrity, and enduring quality rarely found today. Arrive through the oversized garage or elegant French door entry and experience the homes timeless architectural character. The formal living room features hardwood floors, crown molding, and a striking corner brick-surround wood-burning fireplace, while the adjoining dining room showcases chair railing, box wainscoting, and crown molding. The distinguished kitchen is designed for both everyday living and

Welcome to a home as distinctive as Breezy Point itself! Renovated approximately 10 years ago, this 3-bedroom, 3-full-bath coastal home offers approximately 2,425 square feet of finished living space across three levels and a surprisingly functional floor plan filled with character. The heart of the home is the impressive chefs kitchen, featuring generous stone countertops, a large island, stainless steel appliances, a professional-style gas range and abundant cabinetry. Hardwood floors flow through much of the main level, which also includes a comfortable living room with a brick fireplace with a wood stove insert, dining room, light-filled sunroom, two bedrooms and a full bath. The entire upper level is dedicated to a spacious and private primary suite with a walk-in closet and tiled bath featuring a walk-in shower. The lower level offers approximately 811 square feet of finished space, including a full bath and plenty of room for entertaining, hobbies or relaxing. Its unforgettable

Price drop! This 3-bedroom, 1.5-bath home offers fresh paint, new carpeting, approximately 1,040 square feet on the main level, and about 800 square feet of finished basement space for a family room, home office, recreation area, or guests. The seller is ready to make a deal! With an acceptable offer, the seller will provide and pay for a brand-new roof, and you can choose the shingle color from the contractors available options. The seller is also offering up to $10,000 in buyer assistance toward allowable closing costs, prepaid expenses, and/or an interest-rate buydown, subject to lender approval. Enjoy convenient access to Chesapeake Beach restaurants, shopping, parks, beaches, and all the Twin Beaches area has to offer. Come take a tour, explore the possibilities, and make this home your own!

New england charm from the second you turn onto ridge rd | dolphins off your shoreline | water views from multiple rooms | private resident beach | community boat launch | marina next door | st. Michaels within view | no flood zone | all major items done | short term rental potential wake up to the chesapeake. With Views of ST. Michael's. Pour your coffee, sink into your living room, and the Bay is right there through the windows and Sail Boats just gliding by. Workboats heading out at first light, sails on the horizon by afternoon, and in the warm months dolphins rolling past just off the shoreline. And it is not one window. You get water views from multiple areas of this home, from the living room, again from the primary suite upstairs, and wide open from the balcony off that top floor. Neeld Estate is one of the last Chesapeake Bay communities in Calvert County that still feels like a small New England town. Quiet lanes, mature trees, terraced gardens, and deer that wander up to the

Welcome to Wyatt's Ridge an exciting new home community nestled in the heart of sought-after Owings, Maryland. With just 20 spacious, wooded homesites, this intimate and private enclave offers the natural beauty, tranquility, and seclusion that today's buyers are searching for, beautifully paired with the exceptional quality craftsmanship and modern design that Schaefer Homes has built its stellar reputation on. For a limited time, take advantage of pre-construction pricing and receive an additional $20,000 in free options when using our preferred Lender and Title Company an extraordinary opportunity to personalize every detail of your brand-new home from the very beginning. Choose from a collection of thoughtfully designed floor plans offering generous living spaces, stunning kitchens, and flexible layouts built to suit the way you live. For those seeking the ease and elegance of main-level living, select plans also offer available first-floor primary suite designs a rare and sought-a

Welcome to this beautifully renovated Cape Cod, ideally situated on a spacious a 0.4 acre lot at the top of a hill in Calvert County! The moment you enter you get that cozy feeling and won't want to leave! The elevated setting brings in abundant natural light throughout the home. Freshly painted and thoughtfully updated, this home offers flexible living space across three levels. The main level features an updated eat-in kitchen with an L-shaped island, creating a highly functional hub for cooking, dining, and entertaining, plus a white glass beverage center refrigerator. The main level also includes a generously sized living room, 2 bedrooms, and 1 full bath. The finished basement offers 1 bedroom and 1 full bath, with its own entrance and the potential to function as an in-law suite or private living area. There is a separate workshop in the basement that allows you to work on projects during the cold weather. The partially finished attic provides additional flexible space with poten

Price Improvement! There is Something for Everyone Here at This Delightful Brick Front Two-Story Colonial Sitting on 4.3 Acres in Convenient Sunderland, Northern Calvert County. This Gorgeous and Well Maintained 4 Bedroom, 3.5 Bath Home Offers 4500 sf Over 3 Levels Including a Fully Finished Walk Out Lower-Level w 2nd Kitchen & Full Bath Perfect for an In-Law or Au Paire Suite. It Offers a Meticulously Maintained Home, Great Spaces for Entertaining, Easy Care Perennial Gardens for Those with a Green Thumb and is an Entertainers Dream with a Deck & an In-Ground Pool. Even the Car Enthusiast in the Family Will Be Happy with Enviable Attached + Detached Garages! The Interior of the Home Features a Comfortable Layout with Oak Hardwood Floors Throughout the Main and Upper Levels, 9' Ceilings, Crown Moulding, Chair Railing, 2 Wood Burning Fireplaces and 1 Pellet Stove, First Floor Office and an Upper-Level Laundry. The Main Level Features a Welcoming Foyer with a Sweeping Hardwood Staircase

Discover the possibilities at 9030 Southern Maryland Blvd. In Owings! This four-bedroom, two-bath ranch-style home, built in 1974, offers a practical layout, finished basement, and approximately. 40-acre lot in Northern Calvert County. With a little TLC, the main level provides comfortable everyday living, while the finished basement expands the homes usable space and offers flexibility for a recreation room, office, guest area, or additional family living space. A rear deck extends the living area outdoors, and the detached storage shed provides convenient storage for lawn and recreational equipment. Energy-conscious buyers will appreciate the homes solar panel system, adding an important efficiency-minded feature to the property. Enjoy the best of both worlds with a more rural Northern Calvert setting while remaining conveniently located one mile south of Dunkirk shopping, dining, schools, public parks and major commuter routes. Both Andrews Air Force Base and Downtown Washington, DC

Introducing Quality Built Homes Lancaster floor plan, beautifully situated on an exceptional 3.72-acre private homesite in highly sought-after Huntingtown! Offering the perfect blend of quality craftsmanship, thoughtful design, and peaceful surroundings, this new construction home is filled with todays most desirable features and finishes. The main level showcases upgraded trim and molding, a cozy gas fireplace, and a beautifully appointed kitchen featuring maple cabinetry, granite/quartz countertops, a center island, and stainless steel appliances. Enjoy the serene, wooded rear yard and the privacy this spacious homesite provides. Upstairs, the impressive primary suite features a luxurious private bath complete with a custom walk-in shower and separate soaking tub. A 2' side extension provides additional living space and enhances the already spacious floor plan. The full unfinished basement offers plenty of opportunity for future living space and includes a bath rough-in, allowing you

Discover the charm of this beautifully maintained ranch-style home, nestled on a generous 1.56-acre lot that backs to serene woods, offering a peaceful retreat from the hustle and bustle. With 2,514 sq. ft. Of thoughtfully designed living space, this residence features four spacious bedrooms and two and a half bathrooms, perfect for both relaxation and entertaining. Step inside to find warm hardwood flooring that flows throughout the main living areas, complemented by an inviting breakfast area that beckons for morning coffee. The well-appointed kitchen includes modern appliances such as a built-in microwave, dishwasher, and electric oven/range, making meal prep a delight. Enjoy the convenience of a main floor laundry with both washer and dryer included. The bathrooms are designed for comfort, featuring a soaking tub and a stall shower, ensuring a spa-like experience at home. Ceiling fans throughout enhance airflow, creating a cozy atmosphere year-round. Outside, the property boasts a